Citation: Liu Xinyu, Gao Xueqin, Jin Xuejun, Zhao Chunhui, Feng Zhonghua, Sui Yue, Zhao Longxuan, Yan Xin. Synthesis, Characterization and Cytotoxic Activity of Novel Oleanolic Acid and Ursolic Acid Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(12): 3227-3235. doi: 10.6023/cjoc201805030 shu

Synthesis, Characterization and Cytotoxic Activity of Novel Oleanolic Acid and Ursolic Acid Derivatives

Liu Xinyu ^a ,
Gao Xueqin ^a ,
Jin Xuejun ^b ,
Zhao Chunhui ^c ,
Feng Zhonghua ^a ,
Sui Yue ^a ,
Zhao Longxuan ^a,c,, ,
Yan Xin ^d,,

a.
School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029
b.
College of Pharmacy, Yanbian University, Yanji 133002
c.
Liaoning Provincial Key Laboratory of Biotechnology and Drug Discovery, Liaoning Normal University, Dalian 116029
d.
Science and Education Department, Internal Medicine-Oncology, Dalian Third People's Hospital Affiliated to Dalian Medical University, Dalian 116200

Corresponding author: Zhao Longxuan, lxzhao@lnnu.edu.cn Yan Xin, xiaoguai_xiaoen@163.com
Received Date: 15 May 2018
Revised Date: 15 June 2018
Available Online: 23 December 2018
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21101067)the National Natural Science Foundation of China 21101067

Figures(6)

Twenty oleanolic acid and ursolic acid derivatives were prepared by a modification at C-28 position via introduction with 1, 5-pentanedioic acid and glycolic acid followed by amidation with amines, such as morpholine, N-methyl piperazine and N-Boc-ethylenediamine. Their in vitro anticancer activities towards A549, MCF-7 and HepG2 cell lines were evaluated by 3-(4, 5-dimethyl-2-thiazolyl)-2, 5-diphenyl tetrazolium bromide (MTT) method. The results indicated that the anticancer activities of olean-2, 12-diene-28-oic acid[1-(2-amino-ethylamino)-1-oxo]ethyl ester (OA-9d), urs-2, 12-diene-28-oic acid[1-(2-amino-ethylamino)-1-oxo]ethyl ester (UA-9d) against A549, MCF-7 and HepG2 cells are obviously better than those of lead compounds. The ability of UA-9d to inhibit the expression of hypoxia inducible factor-1α (HIF-1α) in hepatocellular carcinoma Hep3B cells was determined by hypoxia response element (HRE)-dependent molecular assay. The results showed that UA-9d could effectively inhibit the expression of HIF-1α.
- oleanolic acid,
- ursolic acid,
- cytotoxic activity
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